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Pravastatin

CAS No.
81093-37-0
Chemical Name:
Pravastatin
Synonyms
MEVALOTIN;PRAVACHOL;ELISOR;KOPOSTAT;Pravatatin;PRAVASELECT;PRAVASTATIN;Pravastatin-D9;PRAVASTATIN(RG);EPTASTATIN SODIUM
CBNumber:
CB6317122
Molecular Formula:
C23H36O7
Molecular Weight:
424.53
MDL Number:
MFCD00869375
MOL File:
81093-37-0.mol
MSDS File:
SDS
Last updated:2023-06-08 09:01:57

Pravastatin Properties

Melting point 171.2-173 °C
Boiling point 634.5±55.0 °C(Predicted)
Density 1.21±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility H2O: 19 mg/mL
pka 4.31±0.10(Predicted)
form powder
color white
CAS DataBase Reference 81093-37-0(CAS DataBase Reference)
FDA UNII KXO2KT9N0G
ATC code C10AA03
EPA Substance Registry System 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-.beta.,.delta.,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (.beta.R,.delta,R,1S,2S,6S,8S,8aR)- (81093-37-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09
Signal word  Danger
Hazard statements  H350-H360--H410
Precautionary statements  P273-P260-P314-P501
Hazard Codes  F,C
Risk Statements  11-34
Safety Statements  16-26-36/37/39-45
WGK Germany  2
RTECS  QJ7185000
NFPA 704
0
3 0

Pravastatin price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 10010342 Pravastatin ≥98% 81093-37-0 10mg $32 2023-01-06 Buy
Cayman Chemical 10010342 Pravastatin ≥98% 81093-37-0 25mg $71 2023-01-06 Buy
Cayman Chemical 10010342 Pravastatin ≥98% 81093-37-0 50mg $119 2023-01-06 Buy
Cayman Chemical 10010342 Pravastatin ≥98% 81093-37-0 100mg $205 2023-01-06 Buy
American Custom Chemicals Corporation API0005939 PRAVASTATIN 95.00% 81093-37-0 1MG $157.5 2021-12-16 Buy
Product number Packaging Price Buy
10010342 10mg $32 Buy
10010342 25mg $71 Buy
10010342 50mg $119 Buy
10010342 100mg $205 Buy
API0005939 1MG $157.5 Buy

Pravastatin Chemical Properties,Uses,Production

New Hypolipidemic drugs

Pravastatin is a derivative of Vastatin. It is a new type of hypolipidemic drug. It is especially suitable for primary hypercholesterolemia which is still not controlled by dietary restriction. The drug is statins, developed by Japan Sankyo Pharmaceutical Co. Ltd. and AmericanBristo1-Myers Sguibb Company. It was listed in Japan for the first time in 1989. It is a new drug of Category 4 of western medicine in China, which has a broad market prospect.

Pharmacological action

  • Pravastatin is a cholesterol lowering drug and is a competitive inhibitor of the Hydroxymethyl glutaryl coenzyme A reductaseh (HMG-CoA reductase). The mechanism of action is the same with lovastatin. It can inhibit the synthesis of cholesterol, increase the metabolism of low density lipoprotein (LDL) and reduce the cholesterol. It can also increase the high density lipoprotein (HDL) and reduce triglyceride. The efficacy of this product is the same as lovastatin and statins. It is used for heterozygous familial, non familial hypercholesterolemia and mixed hyperlipidemia, familial hyperlipoproteinemia type III and serum hypertriglyceridemia (type IV).
  • Pravastatin is an open - ring active substance, and its sodium salt is used clinically. Like other statins, this product competitively inhibits HMG-CoA reductase, reduces serum TC, LDL-C and ApoB, also decreases serum VLDL and TG, and increases HDLC and Apo-A, which is similar to lovastatin.

Pharmacokinetics

This product is absorbed orally, and its bioavailability is about 17%. The concentration of the blood drug peak is reached 1 to 1.5 hours after taking the medicine. It can be selectively distributed in liver cells. It is metabolized in the liver, the active metabolite is TK 2.5% ~ 10%. It excretes rapidly. After one oral administration, 20% and 71% is discharged through urine and feces within 96 hours. The half-life is 1.5 to 2 hours.

Adverse reaction

The occasional adverse reaction includes diarrhea, abdominal pain, and gastrointestinal discomfort as well as the rise of aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, lactate dehydrogenase, gamma glutamyl transpeptidase. Other occasional adverse reaction includes the increase of CPK and urea nitrogen and the phenomenon of urine occult blood.

Precaution

  1. The curative effect of homozygous family hypercholesterolemia is poor. During the treatment, the liver function should be checked regularly. If the increase of SGPT and SGOT is equal to or more than three times the normal upper limit and is persistent, the treatment should be stopped. Patients with the history of liver disease or drinking history should be careful in use.
  2. The use of HMG-COA reductase inhibitor class lipid lowering drugs can cause the increase of CPK. If the rise value is 10 times the normal limit, it should be stopped. In the course of use, if the patient has unexplained myalgia, pain, weakness, especially those with discomfort and fever, they should be reported to the doctor immediately.
  3. Other HMG-COA reductase inhibitors such as cyclosporin, fibrinic acid derivatives, nicotinic acid, etc. can increase the incidence of myositis and myopathy.However, if pravastatin is used simultaneously with the above drugs, clinical trials indicates that the incidence of myositis and myopathy will not be increased.

Description

Pravastatin is the third HMG-CoA reductase inhibitor introduced for the treatment of atherosclerosis. Compared with lovastatin and simvastatin launched earlier, pravastatin is equipotent as an HMG-CoA reductase inhibitor in vitro, yet it is reported to be more tissue-selective.

Chemical Properties

Off-white Cryst

Originator

Sankyo (Japan)

Uses

anti-hyperlipoproteinemic, 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor

Uses

antiglaucoma,

Definition

ChEBI: Pravastatin is a carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin. It has a role as a metabolite, an anticholesteremic drug, a xenobiotic and an environmental contaminant. It is a 3-hydroxy carboxylic acid, a hydroxy monocarboxylic acid, a carboxylic ester, a secondary alcohol, a carbobicyclic compound and a statin (semi-synthetic). It is functionally related to a (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid and a (S)-2-methylbutyric acid. It is a conjugate acid of a pravastatin(1-).

Manufacturing Process

Pravastatin was isolated as products of enzymatic hydroxylation by some kinds of microorganisms of [1S-[1-α(R*),7β,8β(2S*,4S*)8αβ]]-2methylbutanoic acid 1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4hydroxy-6-oxo-2))-pyran-2-yl)ethyl]-1-naphthalenic lactone (campactin) or their carboxylic acid or their salts (products of animal metabolism of microorganisms from the genera Nocardia, Streptomyces et cetera).
Pravastatin may be preparated by using the microorganisms of genera Nocardia (method 1) and Mortierella (method 2).
Method 1 Cultivation of Nocardia autotrophica subsp. amethystineCells of Nocardia autotrophica subsp. amethystina FERM P-6183 was inoculated from a slant culture by means of a platinum loop into each of twenty 500 ml Erlenmeyer flasks, each containing 100 ml of a culture medium having the following composition: glucose - 1.0%, peptone - 0.2%, meat extract - 0.1%, yeast extract - 0.1%, corn steep liquor 0.3%, tap water balance..
Shaking was then carried out at 26°C and 220 r.p.m. for 2 days, at which time sodium 2-methyl-8-(2-methyl-1-oxobutoxy)-β,δ-dihydroxy(1S-(1-α(βS*,δ-S*),2-α,6-α,8-β(R*),8a-α))-1-1,2,6,7,8,8ahexahydronaphthaleneheptanoate was added to a final concentration of 0.05% w/v. Incubation was continued at 26°C and 220 r.p.m. for a further 5 days.
Preparation of pravastatin
After completion of the cultivation, the reaction mixture was filtered and the pH of the filtrate was adjusted to a value of 3 by the addition of trifluoroacetic acid. The acidified filtrate was then extracted three times, each with 1 liter of ethyl acetate, to give extracts containing a mixture (6-α and 6-β) of (1S-(1α,β- S*,δ-S*),2-α,8-βR*),8a-α))-1-naphthaleneheptanoic acid 1,2,6,7,8,8ahexahydro-2-methyl-8-(2-methyl-1-oxobutoxy)-β,δ,6-trihydroxy.
This extract was then immediately transferred into a 5% w/v aqueous solution of sodium hydrogen carbonate, and the pH of the mixture was adjusted to a value of 7.0 by the addition of 2 N hydrochloric acid. The mixture was then adsorbed on a Diaion HP-20 column. The column was washed with water and then eluted with 50% v/v aqueous acetone to give a fraction containing (1S(1-α,β- S*,δ-S*),2-α,6-α,8-βR*),8a-α))-1-naphthaleneheptanoic acid 1,2,6,7,8,8a-hexahydro-2-methyl-8-(2-methyl-1-oxobutoxy)-β,δ,6-trihydroxy-, monosodium salt (pravastatin). This was freeze-dried, to give 200 mg of pravastatine.
Method 2 Cultivation of Mortierella maculata nov. spec. E-97 [NCAIM(P)F 001266]
A spore suspension was prepared with 5 ml of a 0.9% sodium chloride solution obtained from a 7-10 day old, malt extract-yeast extract agar slant culture of Mortierella maculata nov. spec. E-97 [NCAIM(P)F 001266] strain able to 6-β-hydroxylate compactin and the suspension was used to inoculate 100 ml inoculum medium PI (glucose-50 g, soybean meal-20 g, in 1000 ml tap water) sterilized in a 500 ml Erlenmeyer flask.
5 liters working volume a bioconversion culture medium is prepared (glucose20 g, glycerine-20 g, soybean meal-20 g, peptone-5 g, potassium dihydrogen phosphate-0.5 g, polypropylene glycol 2000-1 g, in 1000 ml tap water); the components of the culture medium are added corresponding to 5 liters. Then it was sterilized for 45 min at 121°C and seeded with 500 ml of the inoculum culture.
Before sterilization the pH of the medium was adjusted to 7.0 value.
The fermentation was carried out at 28°C, with a stirring rate of 400 rpm andwith an aeration rate from bottom direction 60 liters/hour for 4 days. At the 2nd day after the transfer the culture started to foam heavily, which can be decreased by the addition of further polypropylene glycol 2000. The pH reached 6.3-7.5 by the 4th day. The feeding of the sodium 2-methyl-8-(2methyl-1-oxobutoxy)-β,δ-dihydroxy(1S-(1-α(β- S*,δ-S*),2-α,6-α,8-β(R*),8aα))-1-1,2,6,7,8,8a-hexahydronaphthaleneheptanoate substrate is allowed to be started if the pH of the broth is above 6.3.
Preparation of pravastatinAt the 4th day of the fermentation 2.5 g compactin substrate is added in sterile filtered aqueous solution. Calculated for the volume of the broth 0.51.0% glucose was added into the culture depending on the pH in the form of 50% solution sterilized at 121°C for 25 min in parallel with the substrate feeding. After 24 hours the compactin substrate is consumed from the culture (is detected by HPLC) and was converted to pravastatin. By lyophilization of the aqueous residue 1.3 g pravastatin was obtained. The chromatographically pure product was crystallized from a mixture of ethanol and ethyl acetate. Melting point: 170-173°C (decomp.).

brand name

Pravachol (Bristol-Myers Squibb);Mevalotin.

Therapeutic Function

Antihyperlipidemic

General Description

Pravastatin, sodium 1,2,6,7,8,8a-hexahydro-β,δ,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoate (Pravachol), is the most rapid actingof the three HMG-CoA reductase inhibitor drugs, reachinga peak concentration in about 1 hour. The sodium salt of theβ-hydroxy acid is more hydrophilic than the lactone forms ofthe other two agents, which may explain this property. In addition,the open form of the lactone ring contributes to a morehydrophilic agent, which, in turn, results in less CNS penetration.This explains, in part, why pravastatin has fewer CNSside effects than the more lipophilic lactone ester of this classof agents. Absorption of pravastatin following oral administrationcan be inhibited by resins such as cholestyramine becauseof the presence of the carboxylic acid function on thedrug. The lactone forms of lovastatin and simvastatin are lessaffected by cholestyramine.

Pravastatin Preparation Products And Raw materials

Global( 160)Suppliers
Supplier Tel Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
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career henan chemical co
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SIMAGCHEM CORP
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Baoji Guokang Bio-Technology Co., Ltd.
0917-3909592 13892490616 gksales1@gk-bio.com China 9340 58

View Lastest Price from Pravastatin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Pravastatin USP/EP/BP pictures 2021-08-06 Pravastatin USP/EP/BP
81093-37-0
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
Pravastatin pictures 2021-07-13 Pravastatin
81093-37-0
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Pravastatin pictures 2021-07-10 Pravastatin
81093-37-0
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Pravastatin pictures
  • Pravastatin
    81093-37-0
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Pravastatin pictures
  • Pravastatin
    81093-37-0
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
KOPOSTAT PRAVASTATIN PRAVASELECT ELISOR EPTASTATIN SODIUM (BETA R,DELTA R,1S,2S,6S,8S,8AR)-1,2,6,7,8,8A-HEXAHYDRO-BETA,DELTA,6-TRIHYDROXY-2-METHYL-8-[(2S)-2-METHYL-1-OXOBUTOXY]-1-NAPHTHALENEHEPTANOIC ACID MONOSODIUM SALT (BETAR, DELTAR,1S,2S,6S,8S,8AR)-1,2,6,7,8,8A-HEXAHYDRO-BETA, DELTA,6-TRIHYDROXY-2-METHYL-8[(2S)-2-METHYL-1-OXOBUTOXYL]-1-NAPHTHALENEHEPTANOIC ACID SODIUM (BETA-R,DELTA-R,1S,2S,6S,8S,8AR)-1,2,6,7,8,8A-HEXAHYDRO-BETA,DELTA,6-TRIHYDROXY-2-METHYL-8[(2S)-2-METHYL-1-OXOBUTOXYL]-1-NAPHTHALENEHEPTANOIC ACID NA [1s-[1a(bs,ds),2a,6b,8b(r),8aa]]-1,2,6,7,8,8a-hexahydro-b,d,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoic acid monosodium salt (+)-(3r,5r)-3,5-dihydroxy-7-[(1s,2s,6s,8s,8ar)-6-hydroxy-2-methyl-8-[(s)-2-methylbutyryloxy]-1,2,6,7,8,8a-hexahydro-1-naphthyl]-heptanoic acid 3BETA-HYDROXYCOMPACTIN, NA (3R,5R)-7-[(1S,2R,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxy-heptanoic acid PRAVASTATIN(RG) 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-b,d,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, [1S-[1a(bS*,dS*),2a,6a,8b(R*),8aa]]- 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-b,d,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (bR,dR,1S,2S,6S,8S,8aR)- (9CI) 3b-Hydroxycompactin PRAVASTATIN FREE BASE Pravatatin 3β-Hydroxycompactin Sodium salt sodium(+)-(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8αR)-6-hydroxy-2-methyl-8-[(S)-2-methyl-hutyryloxy]1,2,6,7,8,8α-hexahydro-1-naphthyl]heptanoate (1S,βR,δR,8aβ)-1,2,6,7,8,8a-Hexahydro-β,δ,6β-trihydroxy-2β-methyl-8α-[(S)-2-methyl-1-oxobutoxy]-1β-naphthaleneheptanoic acid Pravastatin-D9 (3R,5R)-3,5-dihydroxy-7-((1S,2S,6S,8S,8aR)-6-hydroxy-2-Methyl-8-(((S)-2-Methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid PRAVASTATIN (CS-514) (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S)-6-hydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (βR,δR,1S,2S,6S,8S,8aR)- Pravastatin USP/EP/BP PravastatinQ: What is Pravastatin Q: What is the CAS Number of Pravastatin MEVALOTIN PRAVACHOL 81093-37-0 81131-76-6 C23H36O7 Biochemicals and Reagents BioChemical D to K Enzyme Inhibitors by Enzyme Enzyme Inhibitors Enzymes, Inhibitors, and Substrates Hydroxymethylglutaryl-CoA Reductase Selektine